((3-((2R,3aS,4S,6S,7aR)-3a-(benzyloxy)-2-methoxy-4-((4-methoxybenzyl)oxy)hexahydro-4H-furo[2,3-b]pyran-6-yl)prop-2-yn-1-yl)oxy)(tert-butyl)diphenylsilane

Base Information

• Chemical Name: ((3-((2R,3aS,4S,6S,7aR)-3a-(benzyloxy)-2-methoxy-4-((4-methoxybenzyl)oxy)hexahydro-4H-furo[2,3-b]pyran-6-yl)prop-2-yn-1-yl)oxy)(tert-butyl)diphenylsilane
• CAS No.: 1141494-29-2
• Molecular Formula: C₄₂H₄₈O₇Si
• Molecular Weight: 692.924
• Mol file: 1141494-29-2.mol

Synonyms:((3-((2R,3aS,4S,6S,7aR)-3a-(benzyloxy)-2-methoxy-4-((4-methoxybenzyl)oxy)hexahydro-4H-furo[2,3-b]pyran-6-yl)prop-2-yn-1-yl)oxy)(tert-butyl)diphenylsilane

Chemical Property of ((3-((2R,3aS,4S,6S,7aR)-3a-(benzyloxy)-2-methoxy-4-((4-methoxybenzyl)oxy)hexahydro-4H-furo[2,3-b]pyran-6-yl)prop-2-yn-1-yl)oxy)(tert-butyl)diphenylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((3-((2R,3aS,4S,6S,7aR)-3a-(benzyloxy)-2-methoxy-4-((4-methoxybenzyl)oxy)hexahydro-4H-furo[2,3-b]pyran-6-yl)prop-2-yn-1-yl)oxy)(tert-butyl)diphenylsilane

There total 14 articles about ((3-((2R,3aS,4S,6S,7aR)-3a-(benzyloxy)-2-methoxy-4-((4-methoxybenzyl)oxy)hexahydro-4H-furo[2,3-b]pyran-6-yl)prop-2-yn-1-yl)oxy)(tert-butyl)diphenylsilane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 52.0%

(3aS,4S,6S,7aR)-3a-benzyloxy-6-(3-tert-butyldiphenylsilyloxyprop-1-ynyl)-4-hydroxy-2-methoxyhexahydro-2H-furo[2,3-b]pyran (1141494-19-0) + p-Methoxybenzyl bromide (2746-25-0) → (3aS,4S,6S,7aR)-3a-benzyloxy-6-(3-tert-butyldiphenylsilyloxyprop-1-ynyl)-2(S)-methoxy-4-para-methoxybenzyloxyhexahydro-2H-furo[2,3-b]pyran (1141494-20-3) + ((3-((2R,3aS,4S,6S,7aR)-3a-(benzyloxy)-2-methoxy-4-((4-methoxybenzyl)oxy)hexahydro-4H-furo[2,3-b]pyran-6-yl)prop-2-yn-1-yl)oxy)(tert-butyl)diphenylsilane (1141494-29-2)

Guidance literature:

(3aS,4S,6S,7aR)-3a-benzyloxy-6-(3-tert-butyldiphenylsilyloxyprop-1-ynyl)-4-hydroxy-2-methoxyhexahydro-2H-furo[2,3-b]pyran; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.0833333h;

p-Methoxybenzyl bromide; With tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 2h;

DOI:10.1002/anie.200805395

Reference yield:

tert-butyl((3-((2S,3aS,5S,6aR,8R,9aS)-8-methoxy-2-(4-methoxyphenyl)tetrahydro-5H,6aH-[1,3]dioxolo[4,5-c]furo[2,3-b]pyran-5-yl)prop-2-yn-1-yl)oxy)diphenylsilane + benzyl bromide (100-39-0) → ((3-((2R,3aS,4S,6S,7aR)-3a-(benzyloxy)-2-methoxy-4-((4-methoxybenzyl)oxy)hexahydro-4H-furo[2,3-b]pyran-6-yl)prop-2-yn-1-yl)oxy)(tert-butyl)diphenylsilane (1141494-29-2)

Guidance literature:

tert-butyl((3-((2S,3aS,5S,6aR,8R,9aS)-8-methoxy-2-(4-methoxyphenyl)tetrahydro-5H,6aH-[1,3]dioxolo[4,5-c]furo[2,3-b]pyran-5-yl)prop-2-yn-1-yl)oxy)diphenylsilane; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.5h; Inert atmosphere;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.orglett.5b00831

Reference yield:

C21H36O7Si → ((3-((2R,3aS,4S,6S,7aR)-3a-(benzyloxy)-2-methoxy-4-((4-methoxybenzyl)oxy)hexahydro-4H-furo[2,3-b]pyran-6-yl)prop-2-yn-1-yl)oxy)(tert-butyl)diphenylsilane (1141494-29-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: chloro-trimethyl-silane; sodium iodide / acetonitrile / 0.33 h / -20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 1.5 h / -78 °C / Inert atmosphere

4.1: triethylamine / dichloromethane / 2 h / -15 °C / Inert atmosphere

5.1: ozone / dichloromethane / -78 °C

5.2: 4 h / -78 - 20 °C

6.1: silver(l) oxide / acetonitrile / 36 h / 20 °C / Inert atmosphere

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

8.1: camphor-10-sulfonic acid / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

9.1: potassium carbonate / methanol / 1 h / 0 °C / Inert atmosphere

10.1: 1H-imidazole / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

11.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

11.2: 2 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; chloro-trimethyl-silane; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; silver(l) oxide; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile; mineral oil;

DOI:10.1021/acs.orglett.5b00831

upstream raw materials:

(3aS,4S,6S,7aR)-3a-benzyloxy-6-(3-tert-butyldiphenylsilyloxyprop-1-ynyl)-4-hydroxy-2-methoxyhexahydro-2H-furo[2,3-b]pyran

p-Methoxybenzyl bromide

3-<(2-Methoxyethoxy)methoxy>propyne

Downstream raw materials:

(2R,3aS,4S,6S,7aR)-3a-benzyloxy-6-(hydroxypropynyl)-2(R)-methoxy-4-para-methoxybenzyloxyhexahydro-2H-furo[2,3-b]pyran